Phosphorus oxide (P4O10) → HCID 54697738, compound

HRID 897214Notes

Reaction equation

HRID 897214 reaction equation
C(O[C:6](=[O:23])[CH2:7][C:8]([N:10]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])(C)(C)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CS(O)(=O)=O>[Cl:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:10]([CH2:11][C:12]([F:13])([F:14])[F:15])[C:8](=[O:9])[CH:7]=[C:6]2[OH:23]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 69736810HCID 69736810, compound

Product 1

HCID 54697738HCID 54697738, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
100 °C

Procedure

N-(4-Chlorophenyl)-N-(2,2,2-trifluoroethyl)malonamic acid t-butyl ester (2.86 g, 8.1 mmol) was dissolved in methane sulfonic acid (50 mL) under argon with stirring prior to treatment with phosphorus pentoxide (0.51 g). The mixture was heated to 100° C. for 25 minutes. Analysis by LC/MS indicated the reaction was complete and the solution was cooled in an ice bath before quenching with ice and deionized water. The product precipitated and was collected by filtration. The filter cake was washed with ice water followed by cold chloroform and dried on high vacuum to give the title compound (1.83 g). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.10 (2H, q, J=9.0 Hz), 5.97 (1H, s), 7.63 (2H, m), 7.79 (1H, m), 12.09 (1H, br s).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. custombefore quenching with ice
  3. customThe product precipitated
  4. filtrationwas collected by filtration
  5. washThe filter cake was washed with ice water
  6. customdried on high vacuum

Sources & evidence

ORD record
ord-4550f3b665b34156b28552d56fb38e62
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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